| 1 | Tue 12 Aug | 251-1 v AFC WimbledonGillingham 1-1 AFC Wimbledon | Carabao Cup First Round |
| 2 | Sat 25 Oct | 251-2 v Salford CityGillingham 1-2 Salford City | Sky Bet League Two |
| 3 | Sat 1 Nov | 252-2 v Newport CountyNewport County 2-2 Gillingham | Emirates FA Cup First Round |
| 4 | Sat 8 Nov | 251-0 v Bristol RoversBristol Rovers 0-1 Gillingham | Sky Bet League Two |
| 5 | Tue 11 Nov | 250-3 v Wycombe WanderersGillingham 0-3 Wycombe Wanderers | EFL Trophy Southern Group G |
| 6 | Sat 15 Nov | 252-2 v Crawley TownGillingham 2-2 Crawley Town | Sky Bet League Two |
| 7 | Sat 22 Nov | 251-1 v BarnetGillingham 1-1 Barnet | Sky Bet League Two |
| 8 | Sat 29 Nov | 253-3 v Shrewsbury TownShrewsbury Town 3-3 Gillingham | Sky Bet League Two |
| 9 | Sat 6 Dec | 250-0 v Colchester UnitedColchester United 0-0 Gillingham | Sky Bet League Two |
| 10 | Sat 13 Dec | 252-2 v BarrowGillingham 2-2 Barrow | Sky Bet League Two |
| 11 | Sat 20 Dec | 251-2 v Fleetwood TownFleetwood Town 2-1 Gillingham | Sky Bet League Two |
| 12 | Fri 26 Dec | 251-1 v Cambridge UnitedGillingham 1-1 Cambridge United | Sky Bet League Two |
| 13 | Mon 29 Dec | 251-1 v Colchester UnitedGillingham 1-1 Colchester United | Sky Bet League Two |
| 14 | Thu 1 Jan | 250-2 v Swindon TownSwindon Town 2-0 Gillingham | Sky Bet League Two |
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